Halogenated diethyltoluenediamines

Patent metadata

Field	Value
Publication number	US-9340487-B2
Application number	US-201113879356-A
Country	US
Kind code	B2
Filing date	Oct 11, 2011
Priority date	Oct 14, 2010
Publication date	May 17, 2016
Grant date	May 17, 2016

Abstract

Disclosed are halogenated diethyltoluenediamines of formula

wherein either R 1 is an amino group and R 2 is chlorine or bromine, or R 2 is an amino group and R 1 is chlorine or bromine, and isomeric mixtures thereof. The halogenated diethyltoluenediamines of formula I are useful as chain extenders for polyurethanes and hardeners for epoxy resins having a relatively long gel time.

First claim

The invention claimed is:

1. A halogenated diethyltoluenediamine of formula

wherein either R 1 is an amino group and R 2 is chlorine or bromine or R 2 is an amino group and R 1 is chlorine or bromine,
and/or an isomeric mixture thereof.

2. The halogenated diethyltoluenediamine of claim 1 , wherein either R 1 is an amino group and R 2 is chlorine or R 2 is an amino group and R 1 is chlorine, and/or an isomeric mixture thereof.

3. The halogenated diethyltoluenediamine of claim 1 , wherein either R 1 is an amino group and R 2 is bromine or R 2 is an amino group and R 1 is bromine, and/or an isomeric mixture thereof.

4. The halogenated diethyltoluenediamine according to claim 1 adapted for use as a chain extender and/or curing agent in production of polyurethane.

5. The halogenated diethyltoluenediamine according to claim 1 adapted for use as a hardener for an epoxy resin.

6. A process for preparing the halogenated diethyltoluenediamine according to claim 2 , comprising reacting a diethyltoluenediamine of formula

wherein either R 1′ is an amino group and R 2′ is hydrogen, or R 2′ is an amino group and R 1′ is hydrogen,
and/or an isomeric mixture thereof,
with chlorine in sulfuric acid.

7. The process of claim 6 , wherein the sulfuric acid is present in an amount of 5 to 50 molar equivalents, based on the amount of diethyltoluenediamine (II).

8. The process of claim 6 , wherein the chlorine is added in an amount of 2 to 10 molar equivalents, based on the amount of diethyltoluenediamine (II).

9. The process of claim 6 , wherein the reacting is conducted at a temperature from 15° C. to 80° C.

10. A process for preparing the halogenated diethyltoluenediamine according to claim 3 , comprising
(i) reacting a diethyltoluenediamine of formula

wherein either R 1′ is an amino group and R 2′ is hydrogen, or R 2′ is an amino group and R 1′ is hydrogen,
and/or an isomeric mixture thereof,
with an acetylating agent to obtain a diacetyl compound of formula

wherein either R 1″ is an acetylamino group and R 2″ is hydrogen or R 2″ is an acetylamino group and R 1″ is hydrogen,
and/or an isomeric mixture thereof,

(ii) brominating said diacetyl compound (III) with hydrobromic acid and hydrogen peroxide to obtain a corresponding brominated diacetyl compound of formula

wherein either R 1′″ an acetylamino group and R 2′″ bromine or R 2′″ an acetylamino group and R 1′″ is bromine,
and/or an isomeric mixture thereof, and

(iii) hydrolyzing said brominated diacetyl compound (IV) to obtain said halogenated diethyltoluenediamine (I).

11. The process of claim 10 , wherein the acetylating agent in (i) is acetyl chloride in the presence of triethylamine.

12. The process of claim 10 , wherein the brominating (ii) is conducted at a temperature of −10 to +20° C.

13. The process of claim 10 , wherein the hydrolyzing (iii) is conducted with hydrochloric acid in methanol.

14. A chain extender and/or curing agent for producing polyurethane comprising the halogenated diethyltoluenediamine according to claim 1 .

15. A polyurethane produced with a chain extender and/or curing according to claim 14 .

16. A hardener for an epoxy resin comprising a halogenated diethyltoluenediamine according to claim 1 .

17. An epoxy resin hardened with a hardener according to claim 16 .

18. The halogenated diethyltoluenediamine according to claim 1 , which is liquid or semi-liquid at room temperature.

19. The halogenated diethyltoluenediamine according to claim 1 , which is an isomeric mixture.

20. A brominated diacetyl compound of formula

wherein either R 1′″ an acetylamino group and R 2′″ is bromine or R 2′″ an acetylamino group and R 1′″ is bromine, and/or an isomeric mixture thereof.

21. The process of claim 6 , wherein the reacting is conducted at a temperature from 20°C. to 60°C.

Assignees

• Ellinger Stefan
• La Delfa Gaetano
• Franzke Constanze
• Lonza Ag

Inventors

• Ellinger Stefan
• La Delfa Gaetano
• Franzke Constanze

Classifications

• C07C209/74

  by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation · CPC title

• C07C211/52 Primary

  the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups · CPC title

• C07C233/43

  having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton · CPC title